Cesium carbonate → 6-{4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}thieno-[2,3-b]pyridine-2-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	6-Chlorothieno[2,3-b]pyridine-2-carbonitrile	HCID 89526332	—
Reactant	4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one	HCID 117612700	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-{4-[(2R)-2-Hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}thieno-[2,3-b]pyridine-2-carbonitrile	HCID 89535529	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-2-one [I-10] (33 mg, 0.11 mmol), 6-chlorothieno[2,3-b]pyridine-2-carbonitrile [I-13] (22 mg, 0.11 mmol), Pd2(dba)3 (21 mg, 0.023 mmol), Xantphos (26 mg, 0.045 mmol), and Cs2CO3 (55 mg, 0.17 mmol) in dioxane (2 mL) was sealed in a microwave tube and purged three times with nitrogen. It was heated to 120° C. for 20 minutes in a microwave reactor. LC showed formation of the title product, which was purified by silica gel flash chromatography. LC-MS (IE, m/z): 449 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08999991B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-ab0c8008544b4753937743639f771478
Source note	uspto-grants-2015_04